Trifluoroacetic acid → HCID 131715831, compound

HRID 2292327Notes

Reaction equation

HRID 2292327 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][C:33]=1[OH:34])[C:5]([NH:7][NH:8][S:9]([NH:12][C:13]([N:15]1[CH2:18][C@H:17]([NH:19]C(=O)OCC2C=CC=CC=2)[C:16]1=[O:30])=[O:14])(=[O:11])=[O:10])=[O:6].[F:35][C:36]([F:41])([F:40])[C:37]([OH:39])=[O:38].C1(SC)C=CC=CC=1>>[F:35][C:36]([F:41])([F:40])[C:37]([OH:39])=[O:38].[NH2:19][C@H:17]1[CH2:18][N:15]([C:13]([NH:12][S:9]([NH:8][NH:7][C:5](=[O:6])[C:4]2[CH:31]=[CH:32][C:33]([OH:34])=[C:2]([OH:1])[CH:3]=2)(=[O:10])=[O:11])=[O:14])[C:16]1=[O:30]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7520ThioanisoleHCID 86742701HCID 86742701, compound

Product 1

HCID 131715831HCID 131715831, compound

Procedure

(S)-[1-[[[[2-(3,4-Dihydroxybenzoyl)hydrazino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester (0.8 g) was added to a mixture of 3 ml of trifluoroacetic acid and 0.75 ml of thioanisole and the mixture was stirred overnight at room temperature. The trifluoroacetic acid was removed in vacuo and the residue triturated with ether to yield 0.5 g of (S)-3-amino-N-[[2-(3,4-dihydroxybenzoyl)hydrazino]sulfonyl]-2-oxo-1-azetidinecarboxamide, trifluoroacetate salt.

Workup

  1. customThe trifluoroacetic acid was removed in vacuo
  2. customthe residue triturated with ether

Sources & evidence

ORD record
ord-9ec0b059ca194e7e972186d6f1aceb56
Source dataset
uspto-grants-1989_01
Patent number
US04801705

Reaction notes

Loading…